ITunes prompting me for an old ID and password to play purchases made with my new account

I have been purchasing music with my current ID since 2007. I have recently noticed though that some music bought with this account will no longer play unless I give a password for an old account (pre-2007). Luckily I have receipts so can prove which account was used. In "Get Info", the old account name is given even though in the receipt, it shows that it was bought with the more recent account.
Anyone had the same issue? Suggestions on how this happened and what to do next?
I am a former MobileMe user but not sure if that has anything to with it.

If you know the account's id and password then you should be able to authorise that account on your Mac's iTunes via the Store > Authorise This Computer menu option - you can have more than one account authorised on a computer's iTunes.
You won't be able to play them with your new account, all content from the store is tied to the account that downloaded it.

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